CA2570201C - Adjuvants contenant des derives d'acide cyclohexane polycarboxylique - Google Patents
Adjuvants contenant des derives d'acide cyclohexane polycarboxylique Download PDFInfo
- Publication number
- CA2570201C CA2570201C CA2570201A CA2570201A CA2570201C CA 2570201 C CA2570201 C CA 2570201C CA 2570201 A CA2570201 A CA 2570201A CA 2570201 A CA2570201 A CA 2570201A CA 2570201 C CA2570201 C CA 2570201C
- Authority
- CA
- Canada
- Prior art keywords
- acid ester
- weight
- dicarboxylic acid
- agents
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002253 acid Substances 0.000 title abstract description 85
- 239000002671 adjuvant Substances 0.000 title abstract description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 98
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 70
- -1 1,2-diisobutylcyclohexane dicarboxylic acid esters Chemical class 0.000 claims abstract description 62
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 21
- 239000000080 wetting agent Substances 0.000 claims abstract description 19
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 45
- 238000005984 hydrogenation reaction Methods 0.000 claims description 32
- 150000001298 alcohols Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004806 diisononylester Substances 0.000 claims description 4
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- 102100035474 DNA polymerase kappa Human genes 0.000 claims description 2
- 101710108091 DNA polymerase kappa Proteins 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 abstract description 60
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- 238000000518 rheometry Methods 0.000 abstract description 22
- 238000006243 chemical reaction Methods 0.000 abstract description 16
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- 229940127557 pharmaceutical product Drugs 0.000 abstract description 7
- 239000000314 lubricant Substances 0.000 abstract description 5
- 239000010687 lubricating oil Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract 11
- 230000001050 lubricating effect Effects 0.000 abstract 2
- MLKRRUCIHFZBDX-UHFFFAOYSA-N 1,2-bis(2-ethylhexyl)cyclohexane Chemical compound CCCCC(CC)CC1CCCCC1CC(CC)CCCC MLKRRUCIHFZBDX-UHFFFAOYSA-N 0.000 abstract 1
- 239000012628 flowing agent Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000000306 component Substances 0.000 description 24
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 16
- 230000000875 corresponding effect Effects 0.000 description 12
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000004014 plasticizer Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 9
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004609 Impact Modifier Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 239000002390 adhesive tape Substances 0.000 description 6
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- 150000003254 radicals Chemical class 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- 231100001261 hazardous Toxicity 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 5
- WWRGKAMABZHMCN-UHFFFAOYSA-N 6-methyloctan-1-ol Chemical compound CCC(C)CCCCCO WWRGKAMABZHMCN-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000005555 metalworking Methods 0.000 description 4
- YCBDLDKYDMUESI-UHFFFAOYSA-N 3-ethyl-4-methylhexan-1-ol Chemical compound CCC(C)C(CC)CCO YCBDLDKYDMUESI-UHFFFAOYSA-N 0.000 description 3
- VRZRVMXNGMZLDB-UHFFFAOYSA-N 3-ethylheptan-1-ol Chemical compound CCCCC(CC)CCO VRZRVMXNGMZLDB-UHFFFAOYSA-N 0.000 description 3
- MWWKESKJRHQWEF-UHFFFAOYSA-N 4-Methyloctan-1-ol Chemical compound CCCCC(C)CCCO MWWKESKJRHQWEF-UHFFFAOYSA-N 0.000 description 3
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- 238000004026 adhesive bonding Methods 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000010730 cutting oil Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
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- 239000002994 raw material Substances 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- NRZVENBFUFCASY-UHFFFAOYSA-N 2-ethyl-4-methylhexan-1-ol Chemical compound CCC(C)CC(CC)CO NRZVENBFUFCASY-UHFFFAOYSA-N 0.000 description 2
- QNJAZNNWHWYOEO-UHFFFAOYSA-N 2-ethylheptan-1-ol Chemical compound CCCCCC(CC)CO QNJAZNNWHWYOEO-UHFFFAOYSA-N 0.000 description 2
- IGVGCQGTEINVOH-UHFFFAOYSA-N 2-methyloctan-1-ol Chemical compound CCCCCCC(C)CO IGVGCQGTEINVOH-UHFFFAOYSA-N 0.000 description 2
- MQQCUZGHANGGIT-UHFFFAOYSA-N 3,4,5-trimethylhexan-1-ol Chemical compound CC(C)C(C)C(C)CCO MQQCUZGHANGGIT-UHFFFAOYSA-N 0.000 description 2
- HBUKPSFSXBTFFW-UHFFFAOYSA-N 3,5-dimethylheptan-1-ol Chemical compound CCC(C)CC(C)CCO HBUKPSFSXBTFFW-UHFFFAOYSA-N 0.000 description 2
- DNHFCNDAPIMDKL-UHFFFAOYSA-N 3,6-dimethylheptan-1-ol Chemical compound CC(C)CCC(C)CCO DNHFCNDAPIMDKL-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- BMDLBCTXXXEROC-UHFFFAOYSA-N 4,5-dimethylheptan-1-ol Chemical compound CCC(C)C(C)CCCO BMDLBCTXXXEROC-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000008028 pharmaceutical plasticizer Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000015504 ready meals Nutrition 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lubricants (AREA)
- Dental Preparations (AREA)
Abstract
Utilisation d'esters d'acide 1,2-cyclohexane dicarboxylique choisi dans le groupe constitué par ester d'acide 1,2-diisobutylcyclohexane dicarboxylique, ester d'acide 1,2-di-(2-éthylhexyl)-cyclohexane dicarboxylique et ester d'acide 1,2-diisononylcyclohexane dicarboxylique dans des adjuvants ou en tant qu'adjuvants choisis dans le groupe constitué des adjuvants suivants: compositions tensioactives choisies parmi adjuvants de fluidité, adjuvants filmogènes, agents antimoussants, inhibiteurs de formation de mousse, agents de mouillage, agents de coalescence et émulsifiants ; lubrifiants choisis parmi les huiles lubrifiantes, les graisses lubrifiantes et les pâtes lubrifiantes ; adjuvants de calandrage ; adjuvants rhéologiques, agents d'extinction pour des réactions chimiques ; agents de stabilisation d'explosifs ; produits pharmaceutiques ; plastifiants dans des adhésifs ; modificateurs de résistance aux chocs et agents de fixation. La présente invention concerne également des compositions tensioactives, des adjuvants de calandrage, des adjuvants rhéologiques, des agents d'extinction pour des réactions chimiques, des agents de stabilisation d'explosifs, des produits pharmaceutiques, des plastifiants dans des adhésifs, des modificateurs de résistance aux chocs et des agents de fixation contenant des dérivés d'acide cyclohexane polycarboxylique.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004029732.0 | 2004-06-21 | ||
DE102004029732A DE102004029732A1 (de) | 2004-06-21 | 2004-06-21 | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
PCT/EP2005/006682 WO2005123821A2 (fr) | 2004-06-21 | 2005-06-21 | Adjuvants contenant des dérivés d'acide cyclohexane polycarboxylique |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2570201A1 CA2570201A1 (fr) | 2005-12-29 |
CA2570201C true CA2570201C (fr) | 2013-12-10 |
Family
ID=35169777
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2570201A Active CA2570201C (fr) | 2004-06-21 | 2005-06-21 | Adjuvants contenant des derives d'acide cyclohexane polycarboxylique |
Country Status (10)
Country | Link |
---|---|
US (1) | US7816553B2 (fr) |
EP (2) | EP1761596A2 (fr) |
JP (1) | JP4714215B2 (fr) |
KR (1) | KR101169821B1 (fr) |
CN (1) | CN1989194A (fr) |
CA (1) | CA2570201C (fr) |
DE (1) | DE102004029732A1 (fr) |
ES (1) | ES2656138T3 (fr) |
MY (1) | MY146104A (fr) |
WO (1) | WO2005123821A2 (fr) |
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JP5107560B2 (ja) * | 2006-11-22 | 2012-12-26 | 日本精化株式会社 | シクロヘキサンジカルボン酸ジエステル及びこれを含有する化粧料又は皮膚外用剤 |
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WO2009065906A2 (fr) * | 2007-11-20 | 2009-05-28 | Cognis Oleochemicals Gmbh | Procédé de fabrication d'une composition organique contenant un n-nonyléther |
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BRPI0820314A2 (pt) * | 2007-11-26 | 2015-05-26 | Basf Se | Processo para produzir espumas de poliuretano integrais, espuma de poliuretano integral, usos de espumas de poliuretano integrais e de cicloexanodicarboxilatos de dialquila |
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-
2004
- 2004-06-21 DE DE102004029732A patent/DE102004029732A1/de not_active Withdrawn
-
2005
- 2005-06-21 KR KR1020067026858A patent/KR101169821B1/ko active IP Right Grant
- 2005-06-21 US US11/630,456 patent/US7816553B2/en active Active
- 2005-06-21 MY MYPI20052816A patent/MY146104A/en unknown
- 2005-06-21 CA CA2570201A patent/CA2570201C/fr active Active
- 2005-06-21 EP EP05769030A patent/EP1761596A2/fr not_active Withdrawn
- 2005-06-21 CN CNA2005800242086A patent/CN1989194A/zh active Pending
- 2005-06-21 EP EP10177776.1A patent/EP2377844B1/fr active Active
- 2005-06-21 JP JP2007517179A patent/JP4714215B2/ja active Active
- 2005-06-21 ES ES10177776.1T patent/ES2656138T3/es active Active
- 2005-06-21 WO PCT/EP2005/006682 patent/WO2005123821A2/fr active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP2377844A2 (fr) | 2011-10-19 |
WO2005123821A2 (fr) | 2005-12-29 |
KR101169821B1 (ko) | 2012-07-30 |
ES2656138T3 (es) | 2018-02-23 |
EP2377844A3 (fr) | 2012-05-16 |
CA2570201A1 (fr) | 2005-12-29 |
JP4714215B2 (ja) | 2011-06-29 |
CN1989194A (zh) | 2007-06-27 |
EP1761596A2 (fr) | 2007-03-14 |
WO2005123821A3 (fr) | 2006-09-08 |
KR20070033362A (ko) | 2007-03-26 |
DE102004029732A1 (de) | 2006-01-19 |
US7816553B2 (en) | 2010-10-19 |
MY146104A (en) | 2012-06-29 |
US20080039646A1 (en) | 2008-02-14 |
EP2377844B1 (fr) | 2017-10-18 |
JP2008503525A (ja) | 2008-02-07 |
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